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Boyfriend Shirts

Explore boyfriend shirts for a relaxed silhouette and an easygoing take on classic shirting. Check individual fit and sizing details to find your preferred balance of length and roominess.

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Women's L.L.Bean Denim Boyfriend Shirt
L.L.Bean Women's L.L.Bean Denim Boyfriend Shirt
A rugged blue cotton denim shirt with an oversized fit, chest pocket, locker loop and curved hem for easy layering.
(0)
$79.95 $79.95
SALE
$79.95 $79.95
SALE
Women's Scotch Plaid Flannel Shirt, Boyfriend
L.L.Bean Women's Scotch Plaid Flannel Shirt, Boyfriend
The softest, long-lasting flannel in an easy, oversized boyfriend shirt.
(0)
$69.95 $69.95
SALE
$69.95 $69.95
SALE
Men's Scotch Plaid Flannel Shirt, Traditional Fit
L.L.Bean Men's Scotch Plaid Flannel Shirt, Traditional Fit
A green plaid shirt in soft 100% cotton Portuguese flannel with authentic tartan, button-down collar.
(20,377)
$59.95 $59.95
SALE
What customers like:
High-quality material
Stylish and versatile
Soft and cozy
Great fit and comfort
Warm and durable
$59.95 $59.95
SALE
Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth
L.L.Bean Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth
A green houndstooth 100% cotton flannel shirt with shearling lining, resisting shrinking, wrinkling and pilling.
(8,393)
$79.95 $79.95
SALE
What customers like:
Great quality
Softness
Warmth
Nice color
Comfortable fit
$79.95 $79.95
SALE

Boyfriend Shirts

Boyfriend Shirts bring a familiar, borrowed-from-the-closet look to personal style, with an easygoing character that feels right at home alongside longtime favorites. The appeal is in the proportions: a little extra room, a less tailored outline, and a look that doesn’t need much fuss. Still, “boyfriend” isn’t a single, standardized fit, so it’s worth looking closely at each shirt’s measurements rather than choosing by the label alone. Start with your usual size and compare the chest, shoulder and length measurements with a shirt you already enjoy wearing. Think about where you like the shoulder seam to sit and where you want the hem to fall. Those details can make the difference between a shirt that feels intentionally roomy and one that simply feels too big.

Choosing among boyfriend shirts is also a matter of noticing the details you’ll appreciate most. A neatly defined collar creates a different impression from a more understated neckline, while pocket placement, cuff shape and the curve of a hem can change the overall look. If you prefer a simple wardrobe, consider how each shirt’s color or pattern relates to the pieces you already reach for. A familiar shade can make a new addition feel like it has always belonged; a different pattern can bring a welcome change without moving far from your own style. Look at both front and back views, and check the listed length rather than relying only on a model photo. For anyone who has loved a shirt’s appearance but found the proportions weren’t quite right, that extra minute spent with the details is worthwhile.

Boyfriend shirts can also be a thoughtful gift for someone who gravitates toward relaxed silhouettes and classic shirt styling. Take your cues from what they already choose: understated or expressive patterns, longer or shorter hems, a closer fit or noticeably more room. Avoid assuming that a boyfriend cut means you should automatically buy a larger size; the intended proportions may already be reflected in the sizing. Review the individual fit notes and care instructions before deciding, especially if the recipient has clear preferences about clothing upkeep. Whether you’re choosing for yourself or someone you know well, the best starting point is personal preference—not a rule about how the style ought to look. Focus on the proportions and details that feel familiar, appealing and genuinely yours.

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